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The pleasuring of a man's penis using your butthole, aka sitting on a penis.
dude 1: Hey did you see that guys crank?
dude 2: Yeah, I totally wanted to jump off my Busa and sideboss him
sideboss by gootboxybox July 7, 2014
Related Words

Clown Sides 

The appearance of a vast amount of pubic hair protruding from beyond the bikini line, resembling the hairdo of Krusty the Klown from, "The Simpsons."
When Holly took off her pants, I assumed that 50 people would have jumped out of her panties based on those clown sides.
Clown Sides by UrbanBurban February 28, 2015

Sanders Sides 

An ongoing YouTube series created by the EX-viner Thomas Sanders.
Me: Aw man Sanders Sides is such a good series!!
Everyone around me: wtf is that??
Sanders Sides by tinajbee November 2, 2019

St. Louis Sidestep 

A slang racing term in which a driver starts out on the outside of a turn and then cuts to a sharp inside line to pass a driver that is near the center of the curve.
Kurt swiftly pulled off yet another St. Louis Sidestep which let him finish in first.

I see both sides like chanel 

A Bisexual statement made famous by Frank Ocean's song "Chanel," and it's supposed to be a metaphor since the Chanel logo has two C's facing opposite ways... c what he did there?
Boi: You gay?
Boi 2: nah fam, I see both sides like chanel

sideshow mel 

minor British sidekick on the Krusty the Clown TV series; infamous for the large bone(species unidentified)caught through his hair(which happens to resemble that of Marge Simpson, only more of a sea green and much shorter, supposedly stuck there due to a gum chewing incident) and for his common loud outbursts
"My opinion is as valid as the next man's!"
More from Urban Dictionary
Literally "dirty" pronounced with a West Indian accent. Can also have a positive connotation, for example Sean Paul's album title "Dutty Rock".
"The girl is pretty but she corrupt and dutty!"

or, in a positive usage:

"Booya! That freestyle was dutty!"
Dutty by J Hall April 3, 2003
Word of the Day on October 1, 2026
korean word for madam, older woman
Ajumma wait a moment
Ajumma by aintnotinbutnice July 5, 2009
Word of the Day on September 30, 2026

Slop Grenade

When someone uses AI to generate a large document, slide deck, or piece of code/software and tosses it over the fence for you to deal with.
Chad: Hey Brent I sent you the new backend API change to review, it’s only 100 files changed.

Brent: he just tossed me a slop grenade
Slop Grenade by Joe Squid September 28, 2026
Word of the Day on September 29, 2026
Short-hand for the word floccinaucinihilipilification, meaning the estimation of something as valueless (encountered mainly as an example of one of the longest words in the English language).
After we broke up, he was floxi to me.
floxi by Dr. Geek May 13, 2009
Word of the Day on September 28, 2026
NYC people who migrate north to Quahog, RI to see the leaves in the fall.
New York and everyone from there can fornicate themselves with an iron stick.
leafers by ss++ February 8, 2005
Word of the Day on September 27, 2026

Respectfully 

Precedes or follows either a gratuitously disrespectful or honest remark, originated in New York City. Used in similar fashion to "no offense" or "to be honest," interchangeably.
Ya mans is wild buns, respectfully. Respectfully he's washed.

After school, The Modells on Jamaica Ave was active. Respectfully.
Respectfully by john quan the first December 20, 2020
Word of the Day on September 26, 2026
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